Potassium Acetate → 7-(6-Methoxy-pyridin-3-yl)-5-(2-methyl-oxazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

HRID 2112981Notes

Reaction equation

HRID 2112981 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([NH2:11])[N:10]=[C:6]2[CH:5]=[C:4]([C:12]2[CH:13]=[N:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[CH:3]=1.N1C=CC=C(B(O)O)C=1.[CH3:29][C:30]1[O:31][CH:32]=[CH:33][N:34]=1.CC([O-])=O.[K+]>CO.C(Cl)(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(N(C)C)=O>[CH3:19][O:18][C:15]1[N:14]=[CH:13][C:12]([C:4]2[CH:3]=[C:2]([C:32]3[O:31][C:30]([CH3:29])=[N:34][CH:33]=3)[N:7]3[N:8]=[C:9]([NH2:11])[N:10]=[C:6]3[CH:5]=2)=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 517044Potassium AcetateHCID 27343783-Pyridinylboronic acidHCID 125476752-Methyl-1,3-oxazoleHCID 866180285-Chloro-7-(6-methoxy-pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

Product 1

HCID 688359877-(6-Methoxy-pyridin-3-yl)-5-(2-methyl-oxazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 31374DimethylacetamideSolventHCID 21584188Chloroform methanolSolvent

Procedure

A mixture of 5-Chloro-7-(6-methoxy-pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine, which may be produced similar to Example 1A but substituting 6-methoxy-pyridine-3-boronic acid for 3-pyridine boronic acid (300 mg, 1.09 mmol), 2-methyl-oxazole (450 mg, 5.4 mmol), [Pd(PPh3)4] (130 mg, 0.11 mmol), KOAc (534 mg, 5.45 mmol) and DMA (4 mL) was microwaved at 200° C. for 15 min. The cooled mixture was taken up in MeOH/CHCl3, filtered through Celite, and then the filtrate was pre-adsorbed on SiO2. Column chromatography (3% MeOH/CHCl3) gave a solid which was triturated with a 1:1 mixture of DCM/hexane. Filtration gave 7-(6-methoxy-pyridin-3-yl)-5-(2-methyl-oxazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine.

Workup

  1. custommay be produced similar to Example 1A
  2. customwas microwaved at 200° C. for 15 min
  3. filtrationfiltered through Celite
  4. customColumn chromatography (3% MeOH/CHCl3) gave a solid which
  5. customwas triturated with a 1:1 mixture of DCM/hexane
  6. filtrationFiltration

Sources & evidence

ORD record
ord-f37c0f3b5bf241ce938ca83840669e6b
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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